Most Helpful Guy

As long as he doesn't leak any personal info on your mom's med info or anyones elses it should be legal but are you okay with your mom poking her nose in on you guys... Knowing that you two are dating...

Not in his place of work. You will have to meet socially, like if he belongs to a gym, you join too. Get to know him first and see how he reacts. If you approach him any other way, it would most probably fail. Be careful not to stalk him, though.